Patent GB-625644-A (GB)
Title: Improvements in glucosidic compounds
IPC: C07H15/04
Filed: 1939-07-17
Abstract: Synthetic glucosides prepared from sugars and halogen alcohols having chains containing from 2 to 5 carbon atoms, after the introduction of high molecular radicles are stated to be useful in the preparation of emulsions of vegetable, animal and mineral oils and fatty acids.  In order to introduce the high molecular radicles, the brom- or chloralkylglucosides may be reacted with carboxylic acids, phenols, proteins such as casein or protalbinic acid, sulphonic acids or amines.  In examples: (1) b -chlorethylglucoside is obtained from glucose and glycolchlorhydrin; (2) a -chlor-b -oxypropylglucoside is obtained from glucose and glycerolchlorhydrin; (3) a mixture of b -chlorethylglucoside and b  - chlorethylgalactoside, obtained from lactic sugar and glycolchlorhydrin is reacted with diamylamine; (4) wood sugar is reacted with glycol chlorhydrin; (5) b -chlorethylglucoside is obtained by heating dried starch and glycolchlorhydrin in the presence of benzenesulphonic acid; (6) b -aminoethylglucoside is acylated by means of stearic acid, lauric acid and abietinic acid chloride; (7) b -chlorethylglucoside is condensed with methylamine and acylated with octylbenzenesulphochloride and oleic acid chloride; (8) b -chlorethylglucoside is condensed with anhydrous oleic acid soap; (9) chloroxypropylglucoside is condensed with chloroctylphenol; (10) b -chlorethylglucoside is condensed with alkali lignin, isobutyllignin and casein; (11) b -aminochlorethylglucoside is reacted with formaldehyde and phenol to give oxybenzylaminoethylglucoside.  The properties of the products may be modified by treatment with alkylene oxides, e.g. epichlorhydrin, chlorhydrins, reactants forming quaternary ammonium salts and aromatic sulphohalides when the product contains nitrogen, inorganic acids, e.g. phosphoric acid, bromine to convert hydroxy groups to carboxylic groups, alkylating agents, aldehydes, including chloraldehydes and ketones, acylchlorides, chloracetic acid and chloroxypropanesulphonic acid.ALSO:Synthetic glucosides are prepared from sugars and halogen alcohols having chains containing from 2 to 5 carbon atoms by effecting the reaction in the presence of acid catalysts, e.g. sulphuric, phosphoric, sulphonic, perchloric and carboxylic acids and acid salts having a dissociation constant below that of hydrochloric acid.  In order to introduce the high molecular radicles, the resulting brom or chloralkyglucosides may be reacted with carboxylic acids, phenols, proteins such as casein or protalbinic acid, sulphonic acids or amines.  In examples: (1) b -chlorethylglucoside is obtained from glucose and glycolchlorhydrin; (2) g -chlor-b -oxypropylglucoside is obtained from glucose and glycerolchlorhydrin; (3) a mixture of b -chlorethylglucoside and b -chlorethylgalactoside, obtained from lactic sugar and glycolchlorhydrin is reacted with diamylamine; (4) wood sugar is reacted with glycol chlorhydrin; (5) b -chlorethylglucoside is obtained by heating dried starch and glycolchlorhydrin in the presence of benzenesulphonic acid; (6) b -aminoethylglucoside is acylated by means of stearic acid, lauric acid and abietinic acid chloride; (7) b -chlorethylglucoside is condensed with methylamine and acylated with octylbenzenesulphochloride and oleic acid chloride; (8) b -chlorethylglucoside is condensed with anhydrous oleic acid soap; (9) chloroxypropylglucoside is condensed with chloroctylphenol; (10) b -chlorethylglucoside is condensed with alkali lignin, isobutyllignin and casein; (11) b -aminochlorethylglucoside is reacted with formaldehyde and phenol to give oxybenzylaminoethylglucoside.  The products are p  wetting and dispersing agents and their properties may be modified by treatment with alkylene oxides, e.g. epichlorhydrin, chlorhydrins, reactants forming quaternary ammonium salts and aromatic sulphohalides when the product contains nitrogen, inorganic acids, e.g. phosphoric acid, bromine to convert hydroxy groups to carboxylic groups, alkylating agents, aldehydes, including chloraldehydes and ketones, acylchlorides, chloracetic acid and chloroxypropanesulphonic acid.  The products are useful in dyeing with substantive, vat and naphthol dyes and in softening, mercerising and shrinking cellulose fibres.ALSO:Synthetic glucosides prepared from sugars and halogen alcohols having chains containing from 2 to 5 carbon atoms, after the introduction of high molecular radicles are stated to be useful for wetting, washing and also in dyeing with substantive, vat and naphthol dyes and in softening, mercerising and shrinking cellulose fibres.  In order to introduce the high molecular radicles, the brom or chloralkylglucosides may be reacted with carboxylic acids, phenols, proteins such as casein or protalbinic acid, sulphonic acids or amines.  In examples: (1) b -chlorethylglucoside is obtained from glucose and glycolchlorhydrin; (2) a -chlor-b -oxypropylglucoside is obtained from glucose and glycerolchlorhydrin; (3) a mixture of b -chlorethylglucoside and b -chlorethylgalactoside, obtained from lactic sugar and glycolchlorhydrin is reacted with diamylamine; (4) wood sugar is reacted with glycol chlorhydrin; (5) b -chlorethylglucoside is obtained by heating dried starch and glycolchlorhydrin in the presence of benzenesulphonic acid; (6) b -aminoethylglucoside is acylated by means of stearic acid, lauric acid and abietinic acid chloride; (7) b -chlorethylglucoside is condensed with methylamine and acylated with octylbenzenesulphochloride and oleic acid chloride; (8) b -chlorethylglucoside is condensed with anhydrous oleic acid soap; (9) chloroxypropylglucoside is condensed with chloroctylphenol, (10) b -chlorethylglucoside is condensed with alkali lignin, isobutyllignin and casein.  Examples are also given of washing cotton and woollen material.  The properties of the products may be modified by treatment with alkylene oxides, e.g. epichlorhydrin, chlorhydrins, reactants forming quaternary ammonium salts and aromatic sulphohalides when the product contains nitrogen, inorganic acids, e.g. phosphoric acid, bromine to oxidize hydroxy groups to carboxylic groups, alkylating agents, aldehydes, including chloraldehydes and ketones, acylchlorides, chloracetic acid and chloroxypropanesulphonic acid.